tert-butyl 1-Methyl-1H-iMidazol-5-ylcarbaMate synthesis

Yield:66787-73-3 32%

Reaction Conditions:

with diphenyl phosphoryl azide;triethylamine in toluene at 70 - 100; for 4 h;

Steps:

5.1 Step 1:

To a solution of 1-methyl-IH-imidazole-5-carboxylic acid (1.00 g, 7.9 mmol) in t-BuOH (15 mL) and toluene (50 mL) were added diphenylphosphoryl azide (2.4 g, 8.7 mmol) and Et3N (1.2 g, 12 mmol). The mixture was heated at 70 °C for 2 h, then 100 C for 2 h. The mixture was concentrated under reduced pressure, then water (20 mL) was added, and the mixture was extracted with EtOAc (3 x20 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase flash chromatography (Welch Ultimate XE-C 18, 40- 70 jim) eluting with a gradient of 10-95% acetonitrile in water to afford tert-butyl (1-methyl-1H- imidazol-5-yl)carbamate as a yellow solid (500 mg, 32%).

References:

WO2017/19804,2017,A2 Location in patent:Paragraph 0300